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1. EP1519927 - METHOD FOR PRODUCING 3,4-DICHLORO-N-(2-CYANO-PHENYL)-5-ISOTHIAZOLE CARBOXAMIDE

Office European Patent Office
Application Number 03732579
Application Date 17.06.2003
Publication Number 1519927
Publication Date 06.04.2005
Publication Kind B1
IPC
C07D 275/02
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
275Heterocyclic compounds containing 1, 2-thiazole or hydrogenated 1,2-thiazole rings
02not condensed with other rings
C07D 275/03
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
275Heterocyclic compounds containing 1, 2-thiazole or hydrogenated 1,2-thiazole rings
02not condensed with other rings
03with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
A01N 43/00
AHUMAN NECESSITIES
01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
43Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
CPC
C07D 275/03
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
275Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
02not condensed with other rings
03with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Applicants BAYER CROPSCIENCE AG
Inventors HIMMLER THOMAS
Priority Data 10228731 27.06.2002 DE
0306361 17.06.2003 EP
Title
(DE) VERFAHREN ZUR HERSTELLUNG VON 3,4-DICHLOR-N-(2-CYANO-PHENYL)-5-ISOTHIAZOL-CARBOXAMID
(EN) METHOD FOR PRODUCING 3,4-DICHLORO-N-(2-CYANO-PHENYL)-5-ISOTHIAZOLE CARBOXAMIDE
(FR) PROCEDE DE PRODUCTION DE 3,4-DICHLORO-N-(2-CYANOPHENYL)-5-ISOTHIAZOLE CARBOXAMIDE
Abstract
(DE)
Nach einem neuen Eintopf-Verfahren wird 3,4-Dichlor-N-(2-cyano-phenyl)-5-isothiazolcarboxamid dadurch hergestellt, dass man a) Isatosäureanhydrid in Gegenwart von Dimethylformamid mit Ammoniakgas umsetzt, b) dann das dabei entstandene Anthranilsäureamid ohne vorherige Isolierung mit 3,4-Dichlor-isothiazolcarbonsäurechlorid in Gegenwart eines Säureakzeptors und in Gegenwart von Dimethylformamid umsetzt und c) anschliessend das dabei entstandene N-[2-(Aminocarbonyl)-phenyl]-3,4-dichlor-isothiazolcarboxamid ohne vorherige Isolierung in Gegenwart von Dimethylformamid mit Thionylchlorid, Phosphoroxychlorid, Phosgen oder Chlormethylen-dimethylammoniumchlorid umsetzt.

(EN)
The invention relates to a novel one-pot method for producing 3,4-dichloro-N-(2-cyano-phenyl)-5-isothiazole carboxamide. According to said method, a) isatoic acid anhydride is reacted with ammonia gas in the presence of dimethylformamide, b) the anthranilic acid amide thus obtained is reacted with 3,4-dichloro-isothiazole carboxylic acid chloride, without being previously isolated, in the presence of an acid acceptor and in the presence of dimethylformamide, and c) the N-[2-(aminocarbonyl)-phenyl]-3,4-dichloro-isothiazole carboxamide thus obtained is reacted with thionyl chloride, phosphorus oxychloride, phosgene or chloromethylene-dimethylammonium chloride, without being previously isolated, in the presence of dimethylformamide.

(FR)
L'invention concerne un nouveau procédé de production dans un seul pot de 3,4-dichloro-N-(2-cyano-phényle)-5-isothiazolcarboxamide. Ce procédé consiste a) à faire réagir de l'anhydride d'acide isatique en présence de diméthylformamide avec un gaz d'ammoniac puis b) puis à faire réagir l'amide d'acide anthranilique ainsi engendré sans isolation préalable avec du chlorure d'acide 3,4-dichloro-isothiazolcarbonique en présence d'un récepteur d'acide et en présence de diméthylformamide et enfin c) à faire réagir le N-[2-(aminocarbonyle)-phényle]-3,4-dichloro-isothiazolcarboxamide sans isolation préalable en présence de diméthylformamide avec du chlorure de thionyle, de l'oxychlorure de phosphore, du phosgène ou du chlorométhylène-dimélthylammoniumchlorure.